ASYMMETRIC ALDOL REACTIONS OF CHIRAL NI(II)-COMPLEX OF GLYCINE WITH ALIPHATIC-ALDEHYDES - STEREODIVERGENT SYNTHESIS OF SYN-(2S)-BETA-ALKYLSERINES AND SYN-(2R)-BETA-ALKYLSERINES

被引：99

作者：

SOLOSHONOK, VA ^{[1
]}

AVILOV, DV ^{[1
]}

KUKHAR, VP ^{[1
]}

TARAROV, VI ^{[1
]}

SAVELEVA, TF ^{[1
]}

CHURKINA, TD ^{[1
]}

IKONNIKOV, NS ^{[1
]}

KOCHETKOV, KA ^{[1
]}

ORLOVA, SA ^{[1
]}

PYSAREVSKY, AP ^{[1
]}

STRUCHKOV, YT ^{[1
]}

RAEVSKY, NI ^{[1
]}

BELOKON, YN ^{[1
]}

机构：

[1] RUSSIAN ACAD SCI,AN NESMEYANOV ORGANOELEMENT CPDS INST,MOSCOW,RUSSIA

来源：

TETRAHEDRON-ASYMMETRY | 1995年 / 6卷 / 07期

关键词：

D O I：

10.1016/0957-4166(95)00220-J

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Stereoselectivity of aldol reactions between aliphatic aldehydes and Ni(II)-complex of chiral non-racemic Schiff base of glycine with (S)-o-[N-(N-benzylprolyl)amino]benzophenone (BPB) in the presence of excess of MeONa, has been studied as a function of time, reaction conditions and nature of an aldehyde. Two salient features of the reaction, very high pseudokinetic syn-(2S)-diastereoselectivity, and dependence of thermodynamic syn-(2R)-diastereoselectivity on the steric bulk of an aldehyde side chain, were disclosed and used for efficient (more than 90% de and ee) asymmetric synthesis of both syn-(2S) and syn-(2R)-3-alkyl substituted serines. Synthetic potential and reliability of this asymmetric method are demonstrated with the large scale (2-20 g) preparation of enantiomerically pure amino acids.

引用

页码：1741 / 1756

页数：16

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